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The $2,000 an-Hour Woman

In the bedroom, Natalia was a superstar, an escort in demand by Wall Street traders and NFL quarterbacks alike. Her boss, Jason Itzler, who called himself the “King of All Pimps,” wanted to turn his brothel into a Playboy-style national empire, with Natalia as its crown jewel—and his wife. A love story.


Jason Itzler, the self-anointed world’s greatest escort-agency owner, prepared to get down on his knees. When a man was about to ask for the hand of a woman in holy matrimony, especially the hand of the fabulous Natalia, America’s No. 1 escort, he should get down on his knees.

This was how Jason, who has always considered himself nothing if not “ultraromantic,” saw it. However, as he slid from his grade-school-style red plastic seat in preparation to kneel, the harsh voice of a female Corrections officer broke the mood, ringing throughout the dank visitor’s room.

“Sit back down,” said the large uniformed woman. “You know the rules.”

Such are the obstacles to true love when one is incarcerated at Rikers Island, where Jason Itzler, 38 and still boyishly handsome in his gray Department of Corrections jumpsuit, has resided since the cops shut down his megaposh NY Confidential agency in January.

There was also the matter of the ring. During the glorious summer and fall of 2004, when NY Confidential was grossing an average of $25,000 a night at its 5,000-square-foot loft at 79 Worth Street, spitting distance from the municipal courts and Bloomberg’s priggish City Hall, Jason would have purchased a diamond with enough carats to blow the eye loupe off a 47th Street Hasid.

That was when Itzler filled his days with errands like stopping by Soho Gem on West Broadway to drop $6,500 on little trinkets for Natalia and his other top escorts. This might be followed by a visit to Manolo Blahnik to buy a dozen pairs of $500 footwear. By evening, Itzler could be found at Cipriani, washing down plates of crushed lobster with yet another bottle of Johnnie Walker Blue label and making sure everyone got one of his signature titanium business cards engraved with NY Confidential’s singular motto: ROCKET FUEL FOR WINNERS.

But now Jason was charged with various counts of criminal possession of a controlled substance, money laundering, and promoting prostitution. His arrest was part of a large effort by the NYPD and the D.A.’s office against New York’s burgeoning Internet-based escort agencies. In three months, police had shut down American Beauties, Julie’s, and the far-flung New York Elites, a concern the cops said was flying porn stars all over the country for dates. Reeling, pros were declaring the business “holocausted” as girls took down their Websites and worried johns stayed home.

Many blamed Itzler for the heat. In a business where discretion is supposed to be key, Jason was more than a loose cannon. Loose A-bomb was more like it. He took out giant NY Confidential ads in mainstream magazines (the one you’re holding included). In restaurants, he’d get loud and identify himself, Howard Stern style, as “the King of All Pimps.” Probably most fatally, Itzler was quoted in the Post as bragging that he didn’t worry about the police because “I have cops on my side.” After that, one vice guy said, “it was like he was daring us.”

Only days before, Itzler, attired in a $5,700 full-length fox coat from Jeffrey, bought himself a Mercedes S600. Now the car, along with much of the furniture at Jason’s lair, including the $50,000 sound system on which he blared, 24/7, the music of his Rat Pack idol, Frank Sinatra, had been confiscated by the cops. His assets frozen, unable to make his $250,000 bail, Jason couldn’t even buy a phone card, much less get Natalia a ring.

“Where am I going to get a ring in here?” Jason said to Natalia on the phone the other night. He suggested perhaps Natalia might get the ring herself and then slip it to him when she came to visit.

“That’s good, Jason,” returned Natalia. “I buy the ring, give it to you, you kiss it, give it back to me, and I pretend to be surprised.”

“Something like that,” Jason replied, sheepishly. “You know I love you.”

That much seemed true. As Jason doesn’t mind telling you, he has known many women since he lost his virginity not too long after his bar mitzvah at the Fort Lee Community Jewish Center, doing the deed with the captain of the Tenafly High School cheerleader squad. Since then, Jason, slight and five foot nine, says he’s slept with “over 700 women,” a figure he admits pales before the 20,000 women basketball star Wilt “The Stilt” Chamberlain claimed to have bedded. But, as Jason says, “you could say I am a little pickier than him.”

Of these 700 women, Jason has been engaged to nine, two of whom he married. “It was really only one and a half,” Itzler reports, saying that while living in Miami’s South Beach he married “this hot Greek girl. She was gorgeous. The first thing I did was buy her this great boob job, which immediately transformed her from a tremendous A/B look to an out-of-sight C/D look. But her parents totally freaked out. So I got the marriage annulled.”

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